Road-trip stops in Illinois

Cahokia Mounds State Historic Site

The largest pre-Columbian archaeological site north of Mexico — a Mississippian-culture city of 20,000 people that flourished here from 1050 to 1350. UNESCO World Heritage Site. Monks Mound rises 100 feet (climb the stairs for the view back across the river to the Gateway Arch). Interpretive Center is free, the trails are free, and you can do the highlights in two hours. Just across the river from St. Louis, off I-55/70.

Casey, Illinois — Big Things Town

One tiny town with twelve Guinness records and counting. World's largest rocking chair (sit in it, 56 feet up), world's largest mailbox (climb inside), world's largest pitchfork, world's largest golf tee, world's largest wind chime — Casey is two hours of pure delight for under-10s. Free to wander. Bring a paper map of the locations from caseyillinois.com.

Cloud Gate ("The Bean")

Anish Kapoor's 110-ton stainless-steel sculpture in Millennium Park. Kids will spend twenty minutes finding their reflection at different angles — Steve has too. The walk-under arch gives a kaleidoscope view of the Chicago skyline. Free, open every day. Park at Millennium Lakeside garage (entry at Columbus & Monroe) or Grant Park North. Combine with Maggie Daley Park playground across the street for a real kid-friendly Chicago morning before pointing the Truckster south on I-65.

Cozy Dog Drive In

Birthplace of the Cozy Dog — the original corn dog, invented here in 1946 by Ed Waldmire after he saw a sandwich shop in Oklahoma. The 1949 building on the original Route 66 alignment still serves the same recipe his great-grandkids make today. Two Cozy Dogs and a fountain soda is the order. Walls covered in vintage R66 memorabilia. 10 min off I-55 at Springfield.

Emmett Till and Mamie Till-Mobley National Monument

Lewis & Clark National Historic Trail

Lincoln Home National Historic Site

Lou Mitchell's

Chicago breakfast diner that opened in 1923 and sat at the official starting point of Route 66 from 1926 until R66 was decommissioned in 1985. Still serves the legendary Greek-omelet (Lou's father immigrated from Greece) with a side of free milk-doughnut holes that the host hands to women and kids waiting in line. The 'Free Doughnut Hole' tradition has been in place since the diner opened. 50 yards from Chicago Union Station.

Mormon Pioneer National Historic Trail

New Philadelphia National Historic Site

Pullman National Historical Park

Springfield 1908 Race Riot National Monument

The Gemini Giant

Twenty-eight feet of fiberglass astronaut holding a rocket, parked at South Island Park in Wilmington after his big restoration. The original 'Muffler Man' archetype, and one of Route 66's most-photographed roadside icons. Free, photogenic, two-minute stop. The kid asking 'why is there a giant spaceman here?' is exactly the point of a Route 66 detour.

The Silversmith Hotel

Museum of Science and Industry - Chicago

If Chicago is your starting point, the Museum of Science and Industry is the greatest send-off a road trip can have. A real U-505 submarine you walk through, a coal mine descent, a working model railroad, and the baby chick hatchery where your kids watch chicks break out of eggs. Your family will need to be dragged out. It's on the lakefront in Hyde Park, which means Chicago traffic on both ends, but the museum itself is worth every minute of the merge.